This article is cited in 4 papers

Communications

A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione

A. Z. Al'mukhametov, A. M. Gimazetdinov, M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: The title compound, as the new chiral building block for bioactive cyclopentenones, was prepared in 8 steps with 15% overall yield. The key steps involve selective homologation in intermediate [(1S,2R,5R)-5-trimethysilylcyclopent-3-ene- 1,2-diyl]dimethanol by regioselective silylation followed by oxidation and the Wittig reaction.

Keywords: bicyclic δ-lactones, cyclopentenones, bioactive compounds, cyclopentanoids, asymmetric synthesis, lactonization, epoxidation, allylsilanes, silylation, ion-exchange resins..

Language: English

DOI: 10.1016/j.mencom.2020.01.003

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